The 3 Most Important Words in a Founder’s Vocabulary

I have always been amazed by people’s unwillingness to utter the words “I don’t know.” These three words have been, by far, the most important words in the course of my professional development. I remember working for a Hedge Fund when I was a sophomore in College, and being tasked with maintenance of a model that one of my bosses had developed to track financial performance of distressed public companies. I had “sold” my way into this internship leaning heavily on my previous “experience” interning at a Broker/Dealer in high school, but the truth of the matter was, I had no fucking idea what the numbers in this model meant. My high school internship had consisted of running tickets on a trading floor and picking up breakfast for a bunch of Boiler Room brokers. While I did get a taste for the “excitement of the markets,” I received absolutely no background in accounting, could not read a financial statement, and was ill equipped to be updating and “analyzing” the data in this model.

I spent about 2 weeks faking my way through this task (while working hard to add value in other places where I was more confident), and then I realized how inefficient it was for me to be performing it with my limited knowledge. I remember coming clean with my then boss, and saying, “I don’t know what any of these numbers mean.” I expected him to be extremely disappointed, but instead he sat down with me, spent a few hours explaining the basics, and I became infinitely more dangerous and valuable to the Company. I internalized that lesson early, and now I apply it on a regular basis.

Admitting that you don’t know something is by far the fastest way to learn it. When I got to General Catalyst Partners, I literally did not know the difference between an application and an operating system. I had to learn a whole new language, and the way I did it was by writing down every single word and concept I didn’t know, most of which were extremely basic and revealed my complete lack of experience, and then I would corner people in their offices and ask them to explain the items on my list. For about three months I was the kid who didn’t know anything, and then for the next two years I was able to speak intelligently across just about every industry and market to which we paid attention. I remember watching the learning curve of one of the guys who joined our team after me, and it was so much slower than it should have been. I realized the reason was because he never asked for anyone’s help. Never admitted when he didn’t know something, but instead sort of nodded his way through conversations about subjects he hadn’t learned. Had he sucked it up and admitted what he didn’t know up front, his learning curve would have been much steeper.

Especially as a non-tech founder (and as a tech investor) I am constantly dealing in realms where my domain expertise is a fraction of the folks’ with whom I work. SEO is a great example of an area where I lack the necessary domain expertise to be dangerous. I could either keep on referencing SEO as a strategy we are going to implement at JumpPost, without understanding how it works, or admit that I get conceptually why Search Engine Optimization is important, but to be honest, I have an extremely cursory understanding of how it works. As soon as I admit that, while potentially unimpressive to the investor with whom I am speaking, or the potential hire with whom I am recruiting, I am now able to sit back and listen as they explain the three pieces of “low hanging fruit” we can achieve while knowing nothing about SEO, as well as the three more complex concepts around the relationship between SEO and Product architecture that I can now implement during the build of our product. The alternative, of course, being that I could gloss over this “blind spot,” notice in 6 months that we are stinking it up on organic search traffic, and then admit that we don’t really understand SEO, at which point I’ll have to explain to said investor why I just wasted $XX of his investment building a non-SEO friendly product that now needs to be rebuilt/augmented at an additional expense to the Company.

When you expose a “blind spot” in your skill set/knowledge base, those who are in a position to teach don’t feel any need to impress you with their knowledge. Rather they speak to you like they would a first grader, which is exactly where you need to start when you are learning a new language. Imagine trying to learn Italian by sitting in an a 3rd year Italian course. It would be nearly impossible and you would immediately raise your hand and say “I think I’m in the wrong class, where’s Italian 1?” If you’re a non-tech founder, for example, not raising your hand when designing a product with your lead developer and saying “Where’s PHP 101?” is simply stupid. Your job may not be to write the code, but if you don’t understand the basics behind every layer of your product, how can you recruit intelligently, weight the effort of your design against internal resources, and contribute ideas to the development process in a method that is easily digestible to the rest of the team. Even in areas where you don’t need to become an expert in your Company, taking the time to learn the basic principles behind everyone’s efforts is essential for effective communication both within your Company and with parties outside of it.

Beyond product, this practice applies to marketing, fundraising, business development, and every other effort that you are pushing forward in your Company. I remember negotiating a business development agreement with Citigroup in my last company. I identified a natural partner for our business, got in front of the right people to pitch it, and got their verbal commitment to move forward with a deal. We sort of lingered in that realm of “ok, so we want to work together” for a couple of weeks, and then I realized that I didn’t know how to turn that sentiment into action. I remember calling Brad Handler, who is the founder of Exclusive Resorts (and at the time a very important potential investor and business development prospect himself) and telling him “listen, I have this deal with Citigroup that is within reach, but I don’t know what to do now.” He taught me how to write and deliver an LOI (Letter of Intent), described the process of turning that LOI into an Agreement, and coached me on how to get the deal across the finish line. Now, in the course of acquiring this knowledge, I exposed our inexperience to one of the most valuable companies for the future of our business, but I only had to do that once, and every business development effort I encountered from that point forward I came at from a position of strength.

So the moral of the story is, don’t fake it. When you don’t know something, admit it confidently, learn it, and move forward.

this is a great, and dare i say it, somewhat inspiring post.. though i might add that many times in my experience, doing the homework yourself to find out something is never quite the same as asking an expert, and the latter is always the most time-saving option. yet, when i was in the navy i always found it especially difficult to ask the people i supervised for their practical advice on medical issues that i only had a theoretical knowledge of. but at the same time, once i could put my ego aside, it ended up being a great and easy way way to make your employees /subordinates feel valuable to you and engender more of a team-oriented culture.